Indoline → 2,3-Dihydro-1-(2-hydroxypropyl)indole

HRID 8103

Reaction equation

HRID 8103 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH2:10]1[O:13][C@H:11]1[CH3:12]>C(O)C>[OH:13][CH:11]([CH3:12])[CH2:10][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 10328IndolineHCID 146262(2S)-2-Methyloxirane

Product 1

HCID 220147942,3-Dihydro-1-(2-hydroxypropyl)indoleYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,3-dihydro-1H-indole (5.74 g, 48.2 mmol), and (S)-propylene oxide (2.8 g, 48.2 mmol) in ethanol (200 mL) is heated at reflux for 18 hours. The resulting mixture is cooled to room temperature, and evaporated to give a crude oil. The material is purified by flash chromatography (25% ethyl acetate/hexanes) to give 5.37 g (63%) of 2,3-dihydro-1-(2-hydroxypropyl)indole.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 18 hours
  3. customevaporated
  4. customto give a crude oil
  5. customThe material is purified by flash chromatography (25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f19b2da9cf8f4cdb9a4858498d10bf19
Source dataset
uspto-grants-2006_08
Patent number
US07087635B2

Linked notes

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